Diethyl Ether → 1-(2-Chloropyridin-4-yl)ethan-1-one

To a stirred solution of 34.6 g. (0.25 mole) of 2-chloroisonicotinonitrile in 500 ml. of dry ether under a nitrogen atmosphere was added dropwise over 15 minutes 166 ml. of 3.0 M (0.5 mole) solution of methyl magnesium bromide. After stirring at room temperature for 24 hours the precipitate was filtered and added immediately to a mixture of 600 g. of ice and 300 ml. of water to which had been added 150 ml. of 6 N hydrochloric acid. The aqueous phase was extracted (4×100 ml.) with ether and the combined ether extracts dried and concentrated to an oil. The residual oil was extracted with warm petroleum ether (4×50 ml.) and the extracts combined and cooled in a dry ice/acetone bath. The resulting precipitate was filtered and dried to give 21.3 g. (55%) of the desired intermediate, m.p. 36°-38° C.

1. filtrationwas filtered
2. additionadded immediately to a mixture of 600 g
3. additionof water to which had been added 150 ml
4. extractionThe aqueous phase was extracted (4×100 ml.) with ether
5. dry with materialthe combined ether extracts dried
6. concentrationconcentrated to an oil
7. extractionThe residual oil was extracted with warm petroleum ether (4×50 ml.)
8. temperaturecooled in a dry ice/acetone bath
9. filtrationThe resulting precipitate was filtered
10. customdried
11. customto give 21.3 g

ORD record

ord-73b8e45da04e4d8db82964de3151c020

Source dataset

uspto-grants-1981_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04302464